基本情報
- 標準SMILES
C[Si](C)(C)O[Si](C)(C)C- InChIKey
UQEAIHBTYFGYIE-UHFFFAOYSA-N- 分子式
- C6H18OSi2
- 平均分子量
- 162.38 g/mol
- 単同位体質量
- 162.08961826
概要
Hexamethyldisiloxane is an organosiloxane consisting of two trimethylsilyl groups covalently bound to a central oxygen.
名称と識別子
- 優先名称
- Hexamethyldisiloxane
- IUPAC
- trimethyl(trimethylsilyloxy)silane
- 現地名
- ジメチルポリシロキサン
- 英語名
- Dimethicone
- 分子式
- C6H18OSi2
- 分子量
- 162.37752
名称と別名
名称をさらに表示
データベース識別子
- CAS
107-46-0、9006-65-9- PubChem CID
- 24764
- DTXSID
DTXSID4026769- ChEMBL
CHEMBL3184090- ChEBI
CHEBI:78002- UNII
- D7M4659BPU
- EC Number
- 203-492-7
- Nikkaji
- J3.247F
物性
構造計算による物性
- 極性表面積
- 9.2 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 1
- 回転可能結合数
- 2
- 重原子数
- 9
- 形式電荷
- 0
- 複雑度
- 76.2
実験および物理化学的性質
Density
0.7638 at 20 °C
0.76 @ 20°C
Solubility
In water, 0.93 mg/L at 25 °C
0.93 mg/L @ 25 °C (exp)
Boiling Point
99 °C
101 °C @760 [mm Hg]
物理化学的性質
- 比重(密度)
- 1 g/mL · 1 g/mL at 20 °C
- 蒸気圧
- 5 mm · 5 mm Hg ( 20 °C)
- 屈折率
- 20 · n20/D 1.406
- 闪点
- 121 °C · 121 °C
- 貯蔵温度
- Refrigerator
- 溶解性
- 水にほとんど溶けず、無水エタノールに非常に溶けにくいかほとんど溶けず、酢酸エチル、メチルエチルケトン、トルエンと混和します。
- 色
- 無色~濃厚
- 安定性
- 安定。可燃性。強力な酸化剤、還元剤、有機物、酸、塩基とは相容れない。多くの金属を腐食します。
- 主な用途
- 医薬品(低分子化合物)
- 化粧品成分の機能
- 消泡剤肌を保護する皮膚コンディショニング剤 - 保湿剤スキンコンディショニング
- InChI
- InChI=1S/C6H18OSi2/c1-8(2,3)7-9(4,5)6/h1-6H3
- InChIKey
- UQEAIHBTYFGYIE-UHFFFAOYSA-N
- SMILES
- O([Si](C)(C)C)[Si](C)(C)C
- LogP
- 3.646 · 3.646 (est)
- CAS データベース
- 9006 · 9006-65-9
- EPAの化学物質情報
- Dimethicone (9006-65-9)
化学的性質
化学的特性Dimethicones are clear, colorless liquids available in various viscosities. Dimethicone is a fluid mixture of fully methylated linear siloxane polymers end-blocked with trimethylsiloxy units. Methicone is a linear monomethyl polysiloxane. Dimethicone are safe as used in cosmetic formulations, vulcanization.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 0.1% (5 of 3584) of reports.
Danger
H225 (98.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3584 reports by companies from 24 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
危険有害性情報
Regulatory Information
Chemical: Disiloxane, hexamethyl-
Disiloxane, 1,1,1,3,3,3-hexamethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Disiloxane, 1,1,1,3,3,3-hexamethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 15-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15156
Hexamethyldisiloxane: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
An eye irritant; Oral LD50 (rat) = >5000 mg/kg; [HSDB] In a 28-day feeding study of rats, 8 mg/kg/day was the no toxic effect level; Food consumption was decreased and changes were seen in the liver and blood cells in animals fed 640 mg/kg/day; [TSCA Sub-Acute Oral Toxicity Study in Rats] May cause irritation; [MSDSonline]
Special Reports
European Chemicals Bureau; IUCLID Dataset, Hexamethyldisiloxane (107-46-0) (2000 CD-ROM edition). Available from the database query page: http://ecb.jrc.it/esis/esis.php as of July 31, 2006
After the siloxanes class of chemicals was designated to the Interagency Testing Committee (ITC) Priority Testing List, an industry consortium, the Silicones Environmental, Health and Safety Council of North America (SEHSC), worked in cooperation with the ITC and the U.S. Environmental Protection Agency (EPA) to sponsor a voluntary health and safety program for siloxanes. Abstracts of each research report funded through SEHSC are posted under Siloxane Research Program on the SEHSC website [http://www.sehsc.com/srp-research-reports.asp]. The SEHSC also provides information on obtaining full copies of the reports from the EPA on this website.
TSCA Requirements
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hexamethyldisiloxane is included on this list.
Hazard Classes and Categories
Flam. Liq. 2 (98.8%)
Flammable liquids - Category 2
Flammable liquids - Category 2
Skin, Eye, and Respiratory Irritations
Vapors have a very low toxicity for ... humans ... /It/ irritates conjunctiva but does not attack the cornea.
Hexamethyldisiloxane has been noted to give off vapors which are transiently irritating to the conjunctiva, but no injury has been observed.
安全と保護具
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Protective Action Criteria (PAC)
11 [ppm]
120 [ppm]
700 [ppm]
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.2(2) and a regression-derived equation(3), indicates that hexamethyldisiloxane is expected to have slight mobility in soil(SRC). Volatilization of hexamethyldisiloxane from moist soil surfaces is expected to be an important fate process(SRC) given a estimated Henry's Law constant of 0.0453 atm-cu m/mole(4). Hexamethyldisiloxane is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 42.1 mm Hg(5). However, adsorption to soil is expected to attenuate volatilization(SRC). No biodegradation data regarding hexamethyldisiloxane were found; however, dimethyl siloxanes in general are highly resistant to biodegradation(6). As a member of this class biodegradation is not expected to be an important fate process.
TERRESTRIAL FATE: Poly(dimethylsiloxane) (PDMS) fluids in intimate contact with many soils undergo siloxane redistribution and hydrolysis, resulting in the formation of low molecular weight cyclic and linear oligomers. Low molecular weight hydroxy-functional hydrolysis products are water soluble, and the cyclics and trimethylsiloxy-end-blocked oligomers are volatile, thus providing materials which can partition from the soil to the water and atmospheric environmental compartments(1). /Poly(dimethylsiloxane)/
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.2(2) and a regression-derived equation(3), indicates that hexamethyldisiloxane is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 0.0453 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.3 hours and 5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 30 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 340(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Polydimethylsiloxane fluids undergo siloxane bond rearrangement to form low molecular weight linear and cyclic oligomers that are water soluble(8), indicating that hydrolysis of hexamethyldisiloxane may be an important environmental fate process leading to products that will predominantly partition into the atmosphere. No biodegradation data regarding hexamethyldisiloxane were found; however dimethyl siloxanes in general are highly resistant to biodegradation(9). As a member of this class biodegradation is not expected to be an important fate process.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexamethyldisiloxane, which has a vapor pressure of 42.1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hexamethyldisiloxane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 18 days(SRC), calculated from its rate constant of 1.4x10-12 cu cm/molecule-sec at 25 °C(3). Methyl siloxanes are transparent to UV radiation >290 nm(4) and therefore hexamethyldisiloxane is not expected to undergo direct photolytic degradation(SRC).
Effluent Concentrations
Hexamethyldisiloxane was detected in two separate domestic waste sites in Munich Germany at concentrations of 0.01 and 0.31-0.45 mg/cu m(1). Hexamethyldisiloxane was also detected in the respective sewage treatment plants at concentrations of 0.14-0.17 and 0.18-0.20 mg/cu m, respectively(1).
Soil Adsorption/Mobility
The Koc of hexamethyldisiloxane is estimated as 4,600(SRC), using a log Kow of 4.2(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that hexamethyldisiloxane is expected to have slight mobility in soil.
TSCA Test Submissions
The mutagenicity of hexamethyldisiloxane (HMDS) was evaluated in bacterial Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 and yeast Saccharomyces tester strain D4, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. HMDS, diluted in ethanol, was tested for mutagenicity at concentrations up to 5.0 ul/plate using the plate incorporation method. The mutagenicity of HMDS was also tested in bacterial E. coli indicator organisms, although the concentrations used and numerical results were not reported. HMDS did not cause a positive response in any of the bacterial or yeast tester strains, either with or without metabolic activation.
The ability of hexamethyldisiloxane to induce specific locus mutations at the TK locus in cultured L5178Y mouse lymphoma cells (Mouse Lymphoma Mutagenesis Assay) was evaluated in the presence and absence of Aroclor-induced rat liver S9 metabolic activation. Based on preliminary toxicity determinations, both nonactivated and S9 activated cultures were treated with 0.0125, 0.0250, 0.0500, 0.1000, or 0.2000 ul/ml which produced a range of 104 - 32% total growth for nonactivated cultures and from 107 - 0.3% total growth for S9-activated cultures. None of the nonactivated or activated cultures produced mutant frequencies significantly greater than the solvent controls (ethanol).
Hexamethyldisiloxane was examined for DNA modifying activity in Escherichia coli strains W3110 polA+ and P3478 polA- (DNA repair deficiency assay) with and without metabolic activation provided by Aroclor-induced rat liver S9 fraction. The test article did not produce zones of inhibition in either strain when spotted on plates at volumes ranging from 0.001 to 5 ul in the presence or absence of metabolic activation.
The frequency of sister chromatid exchange (SCE) was determined in L5178Y mouse lymphoma cells exposed in vitro to hexamethyldisiloxane with and without metabolic activation provided by mouse liver S9 fraction (induction of liver enzyme activity was not reported). The test article was administered at concentrations of 0.025, 0.05, 0.1 and 0.2 ul/ml in the absence of activation, and at concentrations of 0.025, 0.05 and 0.1 ul/ml in the presence of activation. A statistically significant (students t-test) increase in the mean number of SCE's/cell was observed at 0.05 ul/ml (p < 0.01) in the activated assays, and at 0.025 ul/ml (p < 0.01) and 0.1 ul/ml (p < 0.05) in the nonactivated assays. Statistically significant increases in the mean number of chromosomes/cell with SCE's, and in the mean number of SCE's/chromosome in chromosomes with SCE's were not observed under any condition. The test article was reported to be toxic to cells at concentrations greater than 0.2 ul/ml.
For more TSCA Test Submissions (Complete) data for HEXAMETHYLDISILOXANE (6 total), please visit the HSDB record page.
Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ /Hexamethyldisiloxane/ was submitted to determine its ability to sensitize the skin of normal volunteer subjects using a repeated insult patch test. One-hundred subjects completed the study. Patches were applied to the infrascapular area of the back. The entire study extended over a six week period. It involved three phases: induction, rest, and challenge. The induction phases consisted of nine consecutive applications and subsequent evaluations of the test sites. The rest period lasted fourteen days. The challenge phase used identical patches applied to sites previously unexposed to the test material. Under the conditions employed in this study, there was no evidence of sensitization to the test substance.
/SIGNS AND SYMPTOMS/ Hexamethyldisiloxane has been noted to give off vapors which are transiently irritating to the conjunctiva, but no injury has been observed.
/OTHER TOXICITY INFORMATION/ Vapors have a very low toxicity for ... humans. ... /it/ irritates conjunctiva but does not attack the cornea.
Artificial Pollution Sources
Hexamethyldisiloxane's production and use as a chemical intermediate in the synthesis of silicone fluids, elastomers and fluorosilicone oils as well as in photolithography(1), personal care products and cosmetics(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
AEROBIC: No biodegradation data regarding hexamethyldisiloxane were found(SRC, 2006); however dimethyl siloxanes in general are highly resistant to biodegradation(1). As a member of this class biodegradation is not expected to be an important fate process.
Environmental Bioconcentration
An estimated BCF of 340 was calculated for hexamethyldisiloxane(SRC), using a log Kow of 4.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).
法規制情報
TSCA Requirements
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hexamethyldisiloxane is included on this list.
安全データ
- wgk
- 3
- rtecs
- TQ2690000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 24/25-26
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 9006-65-9(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
Urine is a primary route of elimination of hexamethyldisiloxane (MM) in the form of metabolites. Accordingly, to aid in the pharmacokinetic investigations, major metabolites of MM were identified in urine collected from Fischer rats (F-344) administered (14)C-MM orally and via intravenous injection ... The structural assignments were based on GC-MS analysis of the tetrahydrofuran or methylene chloride extracts of urine containing the metabolites. Some of the metabolites in the extract required protection with trimethylsilyl groups prior to GC-MS analysis using bis(trimethylsilyl)trifluoroacetamide or highly purified hexamethyldisiloxane ... The following are among the major metabolites identified: Me2Si(OH)2; HOMe2SiCH2OH; HOCH2Me2SiOSiMe2CH2OH (predominant); HOCH2Me2SiOSiMe3; HOMe2SiOSiMe3; Me3SiOH. Besides these there were also three other metabolites- HOMe2SiOSiMe2CH2OH, 2,2,5,5- tetramethyl-2,5-disila-1,3-dioxalane and 2,2,5,5-tetramethyl-1,4-dioxa-2,5- disilacyclohexane inferred from GC-MS analyses. Their presence in the HPLC metabolite profile was not established. No parent MM was present in urine. The presence of certain metabolites such as Me2Si(OH)2 and HOMe2SiCH2OH clearly established some demethylation at the silicon-methyl bonds. Metabolites of this linear siloxane are structurally different from that obtained for cyclic siloxanes (D4 and D5) except for the commonly present Me2Si(OH)2. A mechanistic pathway for the formation of the metabolites was proposed.
Major metabolites of hexamethyldisiloxane (MM) a... were identified in urine collected from Fischer (F-344) rats administered (14)C-MM ... orally and via intravenous injection. ... The following are among the major metabolites identified in the case of MM: Me(2)Si(OH)(2), HOMe(2)SiCH(2)OH, HOCH(2)Me(2)SiOSiMe(2)CH(2)OH, HOMe(2)SiOSiMe(2)CH(2)-OH, HOCH(2)Me(2)SiOSiMe(3), and Me(3)SiOH. No parent MM ... was present in urine. The presence of certain metabolites such as HOMe(2)SiCH(2)OH and Me(2)Si(OH)(2) in MM ... clearly established the occurrence of demethylation at the silicon-methyl bonds. Metabolites of the linear siloxane are structurally different from that obtained for cyclic siloxane except for the commonly present Me(2)Si(OH)(2). Mechanistic pathways for the formation of the metabolites were proposed.
Phenyltrimethylsilane given intragastrically to rats was absorbed and eliminated in urine. Three percent of total urinary activity was shown to be from hexamethyldisiloxane.
Absorption, Distribution and Excretion
To examine the distribution of low molecular weight silicones in body organs, separate groups of female CD-1 mice were injected with either breast implant distillate composed primarily of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and tetradecamethylcycloheptasiloxane or a polydimethylsiloxane oil containing low molecular weight linear siloxanes. Mice were injected subcutaneously in the suprascapular area and killed at different times. Levels of individual low molecular weight silicones were measured in 10 different organs (brain, heart, kidney, liver, lung, mesenteric lymph nodes, ovaries, spleen, skeletal muscle, and uterus). In mice treated with the cyclosiloxane mixture and killed at 3, 6, or 9 weeks, highest levels of cyclosiloxanes were found in the mesenteric lymph nodes, ovaries, and uterus, but all organs examined contained cyclosiloxanes. In a cohort killed at 1 year, most organs contained measurable cyclosiloxanes with highest levels in mesenteric lymph nodes, abdominal fat, and ovaries. Of the individual cyclosiloxanes measured, selective retention of decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane relative to octamethylcyclotetrasiloxane was seen in all organs at all time points studied. Organs from animals receiving the linear siloxane mixture were harvested at 9, 12, and 15 weeks. ... Maximum levels in the brain, lungs, and mesenteric lymph nodes /were found/, but all other organs contained measurable levels. These data are, to the best of our knowledge, the first demonstration that after a single subcutaneous injection silicones are widely distributed throughout the body and can persist over an extended period.
用途と製造
Uses
Used to make silicone fluids, elastomers, octamethylcyclotetrasiloxane, and fluorosilicone oils; Also used in cosmetics and in photolithography applications (adhesion promoter/priming agent); [HSDB]
Hydraulic fluid /Organo Silicate MLO 5277/
Chemical intermediate for silicone fluids and elastomers
Hexamethyldisiloxane is used in cosmetic and personal care products, in the production of octamethylcyclotetrasiloxane, as an adhesion promotor-priming agent for photolithography applications, and as an end blocking agent in the production of fluorosilicone oils.
/Used/ ... for headlights ... as a protective layer 20-30 nm thick ... effective diffusion barrier (condensed water resistance is 1000 times greater than without coating) ... . Other applications include the hydrophilic coating of contact lenses and the coating of medical materials to improve biocompatibility.
Used as antifoams in aqueous systems, in petroleum processing, and in laundry detergents ... In human and veterinary medicine ... used as antiflatulent agents ... Useful as lubricants (eg, for films, yarn, medical articles, wine corks, and fillers). /Polydimethylsiloxanes/
U.S. Production
2023: 10,000,000 - <25,000,000 lb
This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
(1977) At least 4.58x10+8 g (est.)
(1986) >1 million-10 million pounds
(1990) >1 million-10 million pounds
For more U.S. Production (Complete) data for HEXAMETHYLDISILOXANE (7 total), please visit the HSDB record page.
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Disiloxane, 1,1,1,3,3,3-hexamethyl-: ACTIVE
... Used as a hydraulic fluid and comes in contact with heated metal surfaces of engines operating at high temperatures. /Organo Silicate MLO 5277/
応用分野
使用dimethicone is a form of silicone used to give products lubricity, slip, and good feel. It can also serve as a formulation defoamer and help reduce the feeling of greasiness that some creams leave on the skin immediately upon application. In addition, dimethicone is reported to protect the skin against moisture loss when used in larger quantities. It improves product flow and spreadability. In combination with other ingredients, dimethicone becomes a good waterproofing material for sunscreen emulsions, and helps reduce the greasiness often seen in high-SPF preparations.
調製方法
Dimethicone isapoly (dimethylsiloxane) obtained by hydrolysis and polycondensation of dichlorodimethylsilane and chlorotrimethylsilane. The hydrolysis products contain active silanol groups through which condensation polymerization proceeds. By varying the proportions of chlorotrimethylsilane, which acts as a chain terminator, silicones of varying molecular weight may be prepared. Different grades of dimethicone are produced that may be distinguished by a number placed after the name indicating the nominal viscosity. For example, ABIL 20 (Evonik Goldschmidt UK Ltd) has a nominal kinematic viscosity of 18–22mm2/s (18–22cSt).
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義本品は、ジメチルポリシロキサンの末端をトリメチルシロキシ基で封鎖した重合体であり、次の化学式で表される。
定義ChEBI: A polydimethylsiloxane macromolecule, composed of dimethylsiloxane repeating units.
関連反応
関連ノート
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